


A bet is a bet!

by LuckyLemonade



Category: Durarara!!
Genre: Awkward Dates, Bets & Wagers, Crossdressing, How Do I Tag, I Wrote This Instead of Sleeping, Izaya Being Izaya (Durarara!!), Lolita, M/M, Mischief, One Shot, Short One Shot, i love him though, izaya being annoying, poor Shizuo
Language: English
Status: Completed
Published: 2020-01-31
Updated: 2020-01-31
Packaged: 2021-02-27 15:14:48
Rating: General Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 843
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/22489258
Author URL: https://archiveofourown.org/users/LuckyLemonade/pseuds/LuckyLemonade
Summary: Izaya loses a bet with his sisters and decides to mess with Shizuo.
Relationships: Heiwajima Shizuo & Orihara Izaya, Heiwajima Shizuo/Orihara Izaya
Comments: 2
Kudos: 50





	A bet is a bet!

**Author's Note:**

> I wrote this at 6am

A ruckus of loud voices came from within the room

"ne Iza-nii! you have to do it! you promised us~"

Izaya had lost a bet with his sisters. . .

"Do i have to? I didn't expect this to be the losing deal. . " 

The informant said in a sulk, glancing over at the bed. There was a set of black thigh highs, a black dress, childish boots and a wig to match his hair colour. 

"You lost the bet fair and square! We wanna see what Iza-nii would look like as a girl!"

He pouted and walked over to the garments, shooing the girls out of the room with a hand gesture. He sighed looking over the dress, it was a simple black dress, lolita styled with a small amount of frills at the bottom, the thigh highs had a cute lace pattern at the end and the boots were quite small and had red bows each side matching his eyes.  
Tossing his signature jacket onto the floor he began to change.  
He slipped the thigh highs on, the dress, the boots and lastly the long wig.

"Im ready!"

The broker shouted to his 2 younger sisters, both of them came running in with pure glee plastered across their face.

"Iza-nii you look super cute! Oh! we should put some makeup on you~!"

"God please no Mairu. ."

"I think it's good idea." 

A quiet voice came from Kururi.

The energetic twin ran to the next room brining in a bag with her.

"I think we should go with a simple dark eye and some mascara~" 

The older brother deciding to comply knowing he wouldn't be able to escape his sisters. 

After many minutes of the sisters messing with his face they finally gave him a mirror to see. 

This actually looks good  
He thought to himself  
I am pretty cute as a girl, ne?

"Do you think i could fool Shizu-Chan with this girls?" 

Both the girls started back at him in surprise not expecting him to say such a thing after the embarrassment. 

"hmmm. . You should totally try it "

Mairu said with a glint of mischief in her eye"

~An hour later~

There's a sound of awe in the streets of Ikebukuro this afternoon. crowds of men are eyeing the new girl in town, she's smoking hot and walks with style. 

Shizuo's grabbing a bite to eat in his favourite bakery.

It doesn't take long for him to notice the girl sticking out like a sore thumb, dressed in all black.  
and she's approaching him. . why?

"You must be the man they call Shiz-ch-, Shizuo Heiwajima~ Blonde hair, bartender suit and glasses?"

Izaya's surprisingly good at pulling off a feminine voice. 

"Yeah I'm him, what do you need?"

"I propose we go on a date~!"

The flea cooed.

"Wh-what? Why me?"

"Well you're known for being the strongest man in Ikebukuro aren't you? I want a strong man who can protect me!"

She clasped her hands together with a forced blush, snuggling up to him.  
The bartender now blushing and pushing her away.

"Alright alright we can go on one date. . .just stop that touchy shit" 

He spits out in a sharp tone. 

"Yay! Meet me at Russia Sushi at 8? Ill pay!"

"S-sure. ."

The girl skipped away, excited for the night coming.

Later that night

The man still dressed in his usual bartender suit waits outside, annoyed by such plans being forced upon him. 

This was a mistake

He sighed within himself, taking a drag of the cigarette resting between his fingers.  
The girl was late, how could she drag him on a date like this and turn up late.  
The sounds of hurried footsteps came around the corner.

"Im sorry im late Shizu-Chan~ i got caught up with some scary thugs, hmph!"

He instantly recognized the horrible nickname, pushing it off as some annoying girly thing. 

"Don't call me that"

"Hmm, why not? I think it's cute!"

"Im not cute."

"Sure you are! Your hair reminds me of an adorable golden retriever, woof!" 

"I'm not some dog!" 

"Hmph well i think it's cute. . Sh. Zu. Chan~!" 

The girl shot back playfully.  
The poor blond getting frustrated with the woman already, dragging her into the restaurant.

"Nice to see you Shizuo-San! i see you have a girl with you, sushi is good! Sushi is love!" 

The Russian man said, flashing a smile. 

They found a booth and ordered their favourites, the girls suspiciously being fatty tuna. 

They finished up quickly, the girl throwing around a few more jokes every now again, although not making much of a conversation and paid the bill. 

"Thankyou for the wonderful night Shizu-Chan" 

She chirped happily to the bartender.  
Giving him a kiss on the cheek.

"I hope we can do this again~!"

The flea suddenly humming in his normal voice, taking of his wig and dashing away gigging.

"That- That fucking bastard was playing me the entire night!" 

Ripping up a vending machine in the process.

"IZAYAAAA!" 

The sound of crashing had permeated the city yet again.

**Author's Note:**

> I didn't really know to end this. . . i hope yall enjohed it though


End file.
